Sales Training Program Jobs in Boston, MA (NOW HIRING)

A Snapshot of WFS Group:

WFS is a high performance RevOps agency that installs and deploys enterprise-grade, AI-driven revenue engines and selling systems for our clients. Think of a lead generation based marketing agency…. But focused on sales 🤪Put simply, our clients outsource their sales department to us and we sell their services to help them scale faster than ever before while changing as many people’s lives as possible. We architect entire end-to-end sales solutions by designing custom sales motions, integrating battle-tested systems, developing go to market strategies powered by our proprietary playbooks, and then hiring, training, and managing a highly trained on demand sales force to deploy faster and more predictable revenue engines. The current verticals we serve are the alternative education space that sell transformative programs including everything from business consulting programs, to programs that teach people how to invest in real estate, learn mergers and acquisitions and many many more, along with the software as a service (SaaS) vertical, bringing cutting edge technology products to market. In short, we’re a full-stack RevOps implementation partner that installs full cycle turnkey selling systems for our clients.

Position Overview:

At WFS Group, we don’t just onboard team members. We deploy high-performance revenue operators into live fire environments with precision and velocity.

The Director of Sales Training sits at the core of our talent activation engine. This role owns the entire learning lifecycle for all new sales hires and ongoing performance development across the organization. From day one ramp to long-term skill stacking, this person ensures every rep is not just “trained,” but fully operational, battle-tested, and continuously evolving.

This is not a passive facilitation role. This is a high-impact, high-ownership leadership function responsible for building, refining, and executing the systems that turn raw talent into revenue producers. You will design onboarding frameworks, lead recurring training cadences, dissect call performance at scale, and continuously optimize the training ecosystem based on real-world performance data.

You are the bridge between strategy and execution, turning sales theory into daily behavioral output that drives measurable revenue outcomes across every brand and account we operate.

You SHOULD apply to this role if:

• You have built or led high-performance sales training or enablement programs

• You understand how to take inexperienced reps and ramp them into consistent closers

• You have deep experience in high-ticket sales environments

• You are equally fluent in coaching soft skills and dissecting hard performance data

• You know how to build training systems that actually stick, not just sound good

• You thrive in fast-moving, high-accountability, no-fluff environments

• You are obsessed with call reviews, performance patterns, and behavioral optimization

• You can design onboarding journeys that shorten ramp time without sacrificing quality

• You understand CRMs, pipelines, and sales metrics at a tactical level

• You are comfortable running live training sessions, workshops, and recurring enablement meetings

• You naturally turn underperformance into structured improvement plans

• You enjoy building order out of chaos and scaling what works

• You are energized by developing talent at scale and watching reps level up quickly

You SHOULD NOT apply if:

• You have never owned or led a sales training or enablement function

• You avoid data and prefer “gut feel” over performance analytics

• You struggle to coach underperforming reps with direct, actionable feedback

• You cannot translate sales performance into structured training content

• You are uncomfortable reviewing calls, pipelines, and rep behavior in detail

• You prefer static environments with minimal change or iteration

• You are not confident running group training sessions or leading rooms

• You get overwhelmed by fast-paced, high-volume sales environments

• You think training is a one-time onboarding event instead of a continuous system

• You are not excited by accountability, metrics, and measurable outcomes

• You lack experience in high-performance sales organizations

• You eat your pizza with ranch (may be flexible on this one)

Major Roles & Responsibilities:

• Own and execute the full onboarding and ramp process for all new sales hires

• Design, build, and continuously improve the WFS Sales Training Center (STC) curriculum

• Lead all new hire training cohorts from kickoff through full ramp completion

• Run recurring weekly and daily enablement sessions for active sales teams

• Develop role-specific training modules for setters, closers, and hybrid roles

• Review sales calls at scale and translate insights into structured coaching frameworks

• Build performance-based feedback loops tied directly to revenue outcomes

• Partner with Sales Directors to identify skill gaps and create targeted interventions

• Continuously refine objection handling, closing frameworks, and discovery processes

• Monitor rep ramp time, conversion rates, and productivity benchmarks

• Standardize best practices across all accounts and ensure adoption across teams

• Collaborate with recruiting and leadership to improve hiring-to-ramp alignment

• Support live deal strategy coaching and real-time performance support

• Maintain and evolve internal training documentation, playbooks, and SOPs

• Identify top performer behaviors and systemize them into repeatable training assets

• Ensure training alignment with CRM data, pipeline structure, and reporting accuracy

• Work cross-functionally with leadership to support scaling initiatives and new account launches

• Drive continuous improvement in sales effectiveness across all WFS brands and teams

Job Type: Full-time, W2

Pay: $120,000-$150,000

Schedule:

• Monday to Friday

Compensation Range: $120K - $150K